What's a fear or insecurity you're working through?

Looking back, what's one decision you made that was a leap of faith? How did it shape where you are today?

If you could alter one decision you made in your early 20s, what would it be?

What aspects of how you were raised do you want to continue on to future generations? What aspects do you want to be sure not to repeat?

What advice would you give about maintaining long-lasting relationships?

If you had to give a TED Talk without any preparation, what topic would you choose?

What was your first job ever?

What's your go-to productivity hack?

What do you think is the best place or way to meet a signifcant other?

Who in life has inspired you the most?

When was the last time you had a difficult conversation? Who was it with, and how did it go?

What is the most ordinary-seeming thing that you find fascinating?

If you were reincarnated as an animal based on your personality, what animal do you think you would come back as?

What's one work-related skill you'd like to develop, and why?

How do you stay productive and motivated when working from home?

If you could have witnessed one event from your family history, what would it be?

How can you take better care of yourself? How will you make that happen?

If the last month were a chapter of your life, what would you title it?

What’s your take on the common career advice to "follow your passion"?

In what ways are you similar to your parents? In what ways are you different?

If you were a dictator of a small country, what crazy dictator things would you do?

What do you think all happy people have in common?

A stranger is inhabiting your body for the day. What are some tips you’d give them?

What's a compliment you recently received?

What's your favorite non valuable item you'll keep to the grave?

What is your best season of the year? Why?

What kind of person do you want to be?

What traits in others are you attracted to?

Who here is is most likely to join the secret service?

What trends do you foresee in your industry in the next five years?

What's a habit you'd like to adopt, but find difficult to stick to?

What actions, if taken, would make you proud of yourself a month from now, regardless of the outcome?

What does your ideal/dream life look like?

What’s one family tradition you want to pass down to your kids?

What's a common myth about your profession that you can debunk?

How has your definition of happiness changed as you've gotten older?

What is one your core principles in life that is guiding you at this time?

On a scale of 1 to 10, how valued do you feel at work?

Who's life do you think you've impacted the most?

What's something you could talk about for hours right now?

What do you feel like you’re really good at?

How would you describe your relationship with yourself in a single word?

What have you been eating lots of lately?

What's a significant professional challenge you overcame in the last year?

Do you think you fit a particular stereotype? Which one, and why?

Did your household ever have a cooking disaster, or a meal that turned out really badly one time?

How do you approach networking, and have you had any success stories?

What do you most need to hear right now, and from whom?

Are human desires endless, and can a society exist without wanting more?

How have you been lately?

Where do you wish you had grown up?

Think of your biggest regret. If you could go back in time and make a decision to keep it from happening, would you?

What's a funny or interesting story from your week?

You're gifted 24 hours where you and your pet(s) are suddenly able to talk to each other. What would you want to tell them, and how would you want to spend your time with them?

What's an unpopular or controversial opinion that you hold?

What's a goal or project you've made progress on?

Is there a particular event or moment that redirected the course of your life? How did it impact you?

What’s one thing that brings you energy and joy lately?

What's the most memorable dream or nightmare you've ever had?

What person in your life do you most admire?

What's a great piece of advice you recently received? Who was it from?

If you could promote one value or ethic in the world, what would it be and why do you think it's vital?

If you had to choose a theme song for your life, what would it be?

What was your "rock bottom"? How did it happen, and how did you get out of it?

How have you stepped out of your comfort zone recently?

Have you been to any cool places lately?

Who in your life do feel is receptive to receiving feedback?

How authentically do you feel you represent yourself to others?

What do you believe is the most significant factor in shaping one's destiny, and how much control does one have over it?

How has your perspective on the world changed in the last five years?

Which relationship in your life do you currently find the most challenging? What are you learning from it?

You have to start a business. If you already have one, it can't be your current one. What would you name it, and what would it do?

What is something you love, that everyone else hates?

What do you have up in your browser tabs right now?

What's something you currently doubt, conciously or subconsciously, that you can do?

What single event or decision do you think most affected the rest of your life? Was there a turning point in your life?

If you could only use five words, how would you describe yourself?

How do you reconcile the pursuit of your personal goals with the need to contribute to the community?

To what degree do you modify your behavior based on who you're with? Do you think this is good or bad?

Do you have any biases you're aware of?

Are there any inner thoughts you have that bother you?

If you were an inanimate object, what would you be and why?

Imagine you could instill one habit in your child that they would carry for life. What habit would you choose and why?

If your life was a genre of music, what would it be?

What's a recent moment in which you feel you represented yourself authentically?

What's one thing you wish you had known when you started your career?

What's something you've recently let go of, and how has it impacted you?

What was your biggest win lately?

What’s something that made you laugh recently?

Can you share an unexpected goal you have for this year?

What do you wish you had done differently in the last month?

Is there anyone who intimidates you? Why do you think this is?

What's one rule you'd put in place if you ruled the world for a day?

Who in your life always makes you laugh?

Who is someone that you recently issued a genuine apology, and what was it for?

What's something you are really into right now?

How would you summarize your last 12 months in one sentence?

How has your perspective on work-life balance evolved over the years, and what influences shaped this?

What kind of a day have you had so far today?

Who has had the most positive impact on your life?